Renewable Production of Nylon-6,6 Monomers from Biomass-Derived 5-Hydroxymethylfurfural (HMF)

Abstract

We report the catalytic conversion of HMF-derived 1,6-hexanediol (HDO) to adipic acid and hexamethylenediamine (HMD) for nylon-6,6 production. Selective oxidation of HDO to adipic acid in yields of ∼90 mol% was achieved with 1 wt% Au/C and 3 wt% Pt/TiO 2 under basic and acidic conditions, respectively. In addition, HDO can undergo oxidative amination to form adiponitrile in selectivity of 66.4 mol% by utilizing a homogeneous iodine-containing organic molecule as oxidant and aqueous ammonia as nitrogen source. Adiponitrile can be subsequently hydrogenated over a Raney nickel catalyst to HMD in close to quantitative yields.